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This report is based on an expert study and findings of related studies on the evolution of threats and challenges in cyberspace with a five-year outlook. The focus is technological and social aspect of current and future web solutions and services in the processes of communication and enhancing living environments in the digital age. We can forecast preservation of the role of the human factor as generator and user of technological innovation, with the consequent cyber threats in the new security environment. Anticipated threats in the 2020 horizon relate to the development of Web 3.0 technologies and 4G/5G communications, with emphasis on protection and control of personal space and data, cloud services, multimedia communication in social media, internet of things, robotic systems with artificial intelligence, and the effects of digital money. This report aims to support the development and the discussions of Bulgaria’s national cybersecurity strategy.